Control of unwanted plants

ABSTRACT

New and valuable process for controlling unwanted plants in important agricultural crops by treating the soil before emergence of the plants and treating the plants postemergence.

United States Patent [1 Fischer 1 CONTROL OF UNWANTED PLANTS [75] Inventor: Adolf Fischer, Mutterstadt, Germany [73] Assignee: Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein, Germany [22] Filed: Mar. 26, 1973 [21] Appl. No.: 344,565

[30} Foreign Application Priority Data UNITED STATES PATENTS 3,210,353 10/1965 Reicheneder et al 71/92 [111 3,861,900 1 Jan. 21, 1975 3,689,507 9/1972 Gates et a1 71/88 FOREIGN PATENTS OR APPLICATIONS 1,434,994 3/1966 France ..71/92 1,419,362 10/1965 France ..71/92 Primary ExaminerGlennon H. Hollrah Attorney, Agent, or Firm-Johnston, Keil, Thompson & Shurtleff [57] ABSTRACT New and valuable process for controlling unwanted plants in important agricultural crops by treating the soil before emergence of the plants and treating the plants postemergence.

1 Claim, N0 Drawings CONTROL OF UNWANTED PLANTS The present invention relates to a process for controlling unwanted plants in important agricultural crops by treating the soil before emergence of the plants and treating the plants postemergence.

wherein R denotes cyclohexyl, or bicycloalkyl or tricycloalkyl of a maximum of 10 carbon atoms, R denotes lower alkyl or alkynyl of a maximum of 4 carbon atoms, and R denotes lower alkyl of a maximum of 4 carbon atoms, or Y b. l-phenyl-4-amino-5-chloropyridazone-(6), or c. a compound of the formula 5 CH3 so mgjca and, after emergence of the unwanted plants, the crop plants and unwanted plants are treated with d. a compound of the'formula where X denotes methyl, and/or e. l-phenyl-4-amino-5-chloropyridazone-(o).

This process ensures that the unwanted plants are destroyed without damage being caused to the crop plants, and it is therefore particularly suitable for controlling unwanted plants-in crops such as rice, groundnuts, cotton, and Indian corn.

The active ingredients are especially effective on di-' cotyledonous seed weeds and monocotyledonous weed grasses, and are therefore suitable for controlling unwanted plants in crops of beet, spinach, potatoes, peas, beans and groundnuts.

Active ingredients a, b, c and e are applied in amounts of l to 5 kg per hectare, preferably 2 to 4 kg per hectare, and active ingredients d in amounts of l to 3 kg per hectare, preferably 1.5 kg per hectare.

Active ingredients a, band c are applied shortly before the crop plants are sown or planted and before emergence of the unwanted plants. They are therefore applied to the soil before the seedlings of the unwanted plants have pierced the surface. The active ingredients may be evenly applied to the soil or incorporated into the upper soil layer and uniformly distributed therein.

NH- CO- O- CH Active ingredients d and/or e are applied after the seedlings of the unwanted plants have pierced the surface. The seedlings develop leaves (seed leaves and genuine leaves) which take up active ingredients d and- /or 2. These active ingredients are evenly applied to the leaves of both crop and unwanted plants for instance in the form of an aqueous spray liquor containing the active ingredient as a solution or suspension.

The active ingredients may be used as solutions, emulsions, suspensions, oil dispersions, granules or dusts. The form of application depends entirely on the purpose for which the agents are being used; in any case it should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosine or diesel oil, further coal-tar oils and oils of vegetable or mineral origin, and cyclic hydrocarbons such as tetrahydronaphthalene and alkylated naphthalenes are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes or wettable powders by adding water. To prepare emulsions the ingredients as such or dissolved in a solvent may be homogenized in water or organic solvents by means of wetting or dispersing agents, e.g., polyethylene oxide adducts. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent. Oils of various types may be added to ready-to-use spray liquors.

Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier, e.g., clay or fertilizers.

Granules may be prepared by bonding the active ingredients to solid carriers.

Directly sprayable dispersions may also be prepared with oils.

The active ingredients may also be mixed with fertilizers, insecticides, fungicides and other herbicides.

EXAMPLE 1 An agricultural plot was sown with the seeds of the plants listed below. Treatment with the active ingredients I ethyl-N-ethyl-N-bicyclo-[2,2,I]-heptylthiol bamate, 0.3 kg per hectare;

II N-lor -2-bicyclo-(3,3,0)-octyl-N-ethylethylthiol carbamate, 0.4 kg per hectare;

III ethyl N-ethyl-N-cyclohexylthio| carbamate, 0.6 kg

per hectare;

IV 3-methoxycarbonylaminophenyl-N-(3'-methylphenyl)-carbamate, 0.4 kg per hectare;

V l-phenyl-4-amino-5-chloropyridazone-(6), 0.5 kg

per hectare;

V IV: 0.25 0.25 kg per hectare,

was carried out as follows:

A with I, II, III, IV, V and V IV before sowing;

B with I, II, III, IV, V and V IV after emergence of the weeds and crop plants;

C with I, II, III and V before sowing combined with IV, V and V IV after emergence of the weeds and crop plants.

The following figures show that the method C gives a better herbicidal action than methods A and B, combined with the same good crop plant compatibility.

car-

Method A v Active ingredient I II III IV V V+lV kg/ha 0.3 0.4 0.6 0.4 0.25+

Crop plants: Beta vulgaris var. crarsa 0 0 O 0 0 0 Beta vulgarir var. allissima 0 0 0 0 0 O Unwanted plants: Sinapis arvensir 3 2 2 0 Chenopudium album 5 2 2 0 3O Pan annua l8 16 I7 0 3 l3 Aloperuru: myoruroides l7 l5 l7 0 2 l2 Avena falua I3 I3 14 0 2 l3 0 no damage I00 complete destruction Method 8 Active ingredient I H W V 025+ kg/ha 0.3 0.4 0.6 0.4 0.5 0.25 Crop plants: Beta vulgari: var. crassa 0 0 0 0 0 0 Beta vulgaris var. allissima 0 0 2 O 0 0 Unwanted plants: Sinapis arvensis 0 0 2 30 Chenopodium album 0 0 2 40 40 Pua annua 8 6 9 Z 6 l5 Alopecurus myosuroides 8 6 9 2 5 l2 Avena fatua 7 5 6 2 5 l0 0 no damage, 100 complete destruction Method C Active ingredient I+lV l+V I+V+IV ll+lV ll+V ll+V+lV 0.3+ 0.4+ kg/ha 0.3+ 0.3+ O.25+ 0.4+ 0.4+ 0.25+

0.4 0.5 0.25 0.4 0.5 0.25 Crop plants: Beta vulgaris var. crassa 0 O 0 0 O 0 Beta vulgari: var. altissima 0 0 0 0 0 0 Unwanted plants: Sinapi: arvensis 70 7O 80 6O 77 Cllenopudium album 60 80 50 55 Pan umma 6O 65 70 4O 45 5O Alopevurur myosuruidz's 50 5O 55 45 48 50 Avena fuluu 45 50 48 43 45 47 0 no damage I00 complete destruction Active ingredient IlI-l-IV lll+V lll+V V+lV V+V V+ V+lV +IV kg/ha 0.6+0.4 0.6+0.5 0.6+ 0.5+ 0.5+ 0.5+

0.25+ 0.4 0.5 025+ 0.25 0.25 Crop plants: Beta vulgaris var. crassa 0 O O O O 0 Beta vulgaris var. alu'rrima 0 0 0 0 0 0 Unwanted plants: Sinapis arvensis 60 65 75 80 Chenopodium album 55 58 78 83 85 Fan annua 55 57 63 45 50 55 Alopecurus myosuroides 53 55 60 40 47 45 Avena falua 50 53 58 40 45 48 O no damage I00 complete destruction EXAMPLE 2 II III: 0.25 0.25 kg per hectare An agricultural plot was sown with the seeds of the plants listed below. Treatment with the active ingredients 2-ethoxy-2,3-dihydro-3 ,3-dimethyl-5- benzofuranylmethanesulfonate, 0.5 per hectare;

Il 3-methoxycarbonylaminophenyl-N-( 3 '-methylphenyl)-carbamate, 0.4 kg per hectare;

III l-phenyl-4-amino-S-chloropyridazone-(6), 0.5 kg

per hectare;

was carried out as follows:

60 A with I, II, III and II III before sowing;

Method A B Active ingredient I II III "H" I II III ll+ 015+ III kglha 0.5 0.4 0.5 0.25 0.5 0.4 0.5 O.Z5+

Crop plants: Beta vulgaris 2.5 0 0 0 4 0 0 0 Unwanted plants: Chenopodium album 3 0 30 40 I0 40 40 60 Sinapis arvensis 4 0 30 I2 50 30 55 Alopecurur myasuroides l7 0 2 I2 2 5 l2 Avena falua l6 0 2 13 ll 2 5 l0 Method C Active ingredient I+II I+|II I+II+III kg/ha 0.5-MA 0.5+O.5 0.5-H).25+O.25 Crop plants: Beta vulgaris 0 0 0 Unwanted plants: Chenopodium album 60 65 80 Sinapis arvensis 70 67 85 Alopecurus myosuroides 50 63 70 Avena fatua 48 55 68 0 no damage I00 complete destruction EXAMPLE 3 IV 3-methoxycarbonylaminophenyl-N-(3'-methylphenyl)-carbamate, 0.1, 1.0 and 1.2 kg/hectare In the greenhouse, loamy sandy soil was filled into 25 wa Carried out as follows:

pots and sown with the seeds of various plants. Treatment with the active ingredients I ethyl N-ethyl-N-cyclohexylthiolcarbamate, 0.l, 1.0

and L2 kg/hectare;

A B C with I, II, III and IV before or after sowing;

with I, II, III and IV after emergence of the weeds; with I II, I III, III II and II before or after sowing and with ll shortly before emergence of the II I-phenyl-4-am|no-5-chloropyridazone-(6), 0.1, L0 se dling and lh IV after emergenCe 0f the and 1.2 kg/hectare; weeds. The results given below show that method Ill 2-ethoxy-2,3-dihydro-3,3-dimethyl-5- C has a better herbicldal action than methods A benzofuranylmethane sulfonate, 0.1, L0 and 1.2 and B, combined with the same good crop plant kg/hectare; compatabrhty.

Method A Active ingredient I II III kg/ha 0.l 1.0 L2 0.1 1.0 L2 0.1 1.0 1.2

Crop plants: Beta vulgaris var. crassa 0 0 0 0 0 0 0 4 4 Beta vulgaris var. altissima 0 0 0 0 0 O (l 4 4 Unwanted plants: Sinapis arvensis 0 8 9 I0 30 0 l0 1 l Chenopodium album 0 7 8 I3 42 43 0 l0 l2 Poa trivialis 2 42 l l7 l7 5 48 50 Alopecurus myosuroides 3 63 0 l2 l3 4 45 47 Avena fatua 2 36 37 0 6 8 2 40 41 Method A Active ingredient IV kg/ha 0.l L0 1.2 Crop plants: Beta vulgaris var. crassa 0 0 0 Beta vulgaris var. altissima 0 0 0 Unwanted plants: Sinapis arvensis 0 0 0 Chenopodium album 0 0 0 Poa trivialis 0 O O Alopecurus myosuroides 0 0 0 Avena fatua 0 0 O I Method B Active ingredient I II kg/ha 0.l 1.0 1.2 0.1 L0 1.2 Beta vulgaris var. crassa 0 0 0 0 0 0 Beta vulgaris var. altissima 0 3 3 O 0 0 Unwanted plants: Sinapis arvensis 0 5 6 I4 35 36 Chenopodium album 0 4 5 8 72 Poa trivialis I l5 l6 2 l2 l3 Alopecurus myosuroides I l5 I6 I 20 21 Avena fatua 0 10 ll 1 I0 I l Method B Active ingredient III IV kg/ha (H 1.0 L2 0.] L0 1.2 Crop plants: Beta vulgaris var. crassa 0 5 6 0 0 0 Beta vulgaris var. altissima 0 5 6 0 0 0 8 Table Continued Method A Active ingredient I ll lll kg/ha 0.] L 1.2 0.1 1.0 L2 0.1 1.0 l.2

Unwanted plants: Sinapis arvensis 2 20 22 8 75 77 Chenopndium album 3 20 2] 85 86 Poa trivialis S 45 46 0 10 ll Alopecurus myosuroides 4 50 52 l 10 Ll Avena fatua 8 50 5| 2 22 Method C Active ingredient (l ll) [V Crop plants: Beta vulgaris var. crassa 0 0 0 Beta vulgaris var. altissima O 0 0 Unwanted plants: Sinapis arvensis I00 70 55 Chenopodium album I00 85 60 Poa trivialis 50 70 Alopecurus myosuroides 56 W 90 Avena fatua 55 42 55 Active ingredient (l lll) IV kg/ha O.l-H).l+l.0 O.l+l.0+0.l l.0+0.l+0.l Crop plants: Beta vulgaris var. crassa 0 4 0 Beta vulgaris var. altissima 0 4 0 Unwanted plants: Sinapis arvensis I00 48 Chenopodium album 100 52 56 Poa trivialis 60 83 75 Alopecurus myosuroides 60 78 I00 Avena fatua 75 72 Method C Active ingredient (lll ll) IV kg/ha 0.l+0.l+l.0 0:l+l .0+0.l l.O+0.l+0.l Crop plants: Beta vulgaris var crassa 0 0 0 Beta vulgaris var. altissima 0 O Unwanted plants. Sinapis arvensis I00 70 Chenopndium album I00 82 Poa trivialis 60 53 82 Alopecurus myosuroides 45 60 80 Avena fatua 53 4O Method C Active ingredient (ll II) W kg/ha O.l+0.l+l.0 0.l+l.0+l.0 l0+0.l+0.l Crop plants: Beta vulgaris var. crassa 0 0 0 Beta vulgaris var. altissima 0 0 0 Unwanted plants: Sinapis arvensis I00 80 Chenopodium album 100 95 Poa trivialis 70 5O 50 Alopecurus myosuroides 45 45 45 Avena fatua 50 40 40 0 no damage I00 complete destruction.

1 claim:

1. A process for controlling the growth of unwanted plants with a combined effective amount of (a) and (b) wherein the soil in which unwanted plant growth is to and, after emergence of the unwanted plants, the crop plants and unwanted plants are treated with (b) l-phenyl-4-amino-5-chloropyridazone-(6) wherein the ratio of (a) to (b) is from about 1:2 to 2:1.

wanted plants with a compound of the formula (a) be prevented is treated before emergence of the un- CH OC H 

